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True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and shocking history exposed where it happened. More thrilling than a ghost tour and more revealing than a history tour, Key West’s underworld comes alive, Key West-style.
Be the next eyewitness. We're bringing crime to the streets!
Wheelchair accessible
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Suitable for all physical fitness levels
Not appropriate for children under the age of 17 years old
For a full refund, cancel at least 24 hours before the scheduled departure time.
A Tour Guide who doubles as an Expert Witness to True Crime
Front-Row Access to History’s Dark Side
Street-level Secrets & Scandals
Historical Crime revived in the streets of Key West
Gratuity for your storytellers
Bail money
Mallory Square
Before sunsets and applause, it was a stage for smuggling and schemes...we start the tour in the Mallory Square area and meander through the streets of Old Town. Be sure to catch the sunset by the water's edge before your tour!
Capt. Tony's Saloon
Where pirates met their end and the floor holds a name you won’t forget...
6 đánh giá
Tổng số đánh giá và xếp hạng từ Viator & TripAdvisor
BrianF567,
12 thg 11, 2025
- Đánh giá từ Tripadvisor
This was a really cool tour...and let me say new tour....here in Key West. Now let me say as a local, I know a lot about Key West and the weird things of Key West....but this tour was very interesting and informative...especially in a fun way. I knew some of the...let say...so called crimes and crazy of Key West, but I learned much more on this tour. I"m not going to spill the beans on a few of the crimes they discuss...but let's just say...it's an eye opening experience. Think you know about Key West and the dark sides those ghost tours talk about....well take this tour and get the real scope on the behind the scenes and juicy stores of those who brought crime in Key West to the next level of the crime world. Your guides will share with you so much information on the crimes, the history and well....let's just leave it there...you take the leap in learning about Key West's criminal crime past. Enjoy everyone!
ericabH8543GD,
11 thg 11, 2025
- Đánh giá từ Tripadvisor
It was a very fun and informative walking tour. Highly recommend if you love true crime and want to learn more about Key West.
Pioneer13148,
11 thg 11, 2025
- Đánh giá từ Tripadvisor
This was a great experience for our family. I would highly recommend doing this while in Key West or even locals would enjoy. Kim was a great guide she was very knowledgeable. Worth the money





joshkS5655IY,
10 thg 11, 2025
- Đánh giá từ Tripadvisor
So much fun!! I knew Key West had some crazy stories but wow! Plus the way they organized the tour and the surprises they had in store for us was fantastic....very creative and clever. When my family and friends come into town I'm definitely going to recommend this!
reverendg2015,
5 thg 11, 2025
- Đánh giá từ Tripadvisor
Loved it, I have lived in Key West for over 20 years... I have only been on 3 waking tours. 1st was a Ghost Tour, everyone does that. 2nd was a David Sloan "Haunted Bathroom" Tour... A once-in-a-lifetime experience. And this one... I have studied the Crimes in Key West for the past 60 years... One might think it's all DUIs, VOP, and Bike Thiefts! But No! Wait, there is More! I had a blast - Our tour guide, Yvonne, made us all Criminals in the first 15 minutes! And it just kept getting Better! Looking forward to "Breaking the Law" with her again soop




dustyhall,
5 thg 11, 2025
- Đánh giá từ Tripadvisor
As we walked the streets of Old Town, our guide explained many interesting crimes that had taken place. The tour was at a casual pace and Yvonne captured everyone's attention with her vivid storytelling.

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